


Pretty Boy

by Anonymous



Series: Her Pets [1]
Category: Original Work
Genre: Coming of Age, Dress Up, F/M, Feminization, M/M, Multi, Shopping, Slice of Life, Sugar Baby, Sugar Mama, Transformation, black mail, cross dressing, femboy, mall
Language: English
Status: Completed
Published: 2020-03-15
Updated: 2020-03-15
Packaged: 2021-02-28 20:48:14
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,876
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23163520
Author URL: https://archiveofourown.org/
Summary: Thomas has a secret.Lily has a hole in her heart.Can the two make it work?
Series: Her Pets [1]
Series URL: https://archiveofourown.org/series/1670305
Comments: 1
Kudos: 18
Collections: anonymous





	Pretty Boy

**Author's Note:**

> This is based on a fantasy I’ve had in real life that involves one of my best friends. I hope they never see this. But I had to write it down. 
> 
> Names have been changed for privacy reasons.

Thomas couldn’t help the smile on his lips as he twirled in the mirror. The fabric of his skirt rising to show off the hint of the panties underneath. The soft material tight against him. He giggled softly, batting his eyelashes at his reflection. The soft gold glitter on his eyelids making his eyes look larger and more innocent. Paired with the off the shoulder crop top. He really looked like a teen girl. 

This was his secret. Something that was meant only for him to know. Over the years he had slowly collected a sizable collection of panties, skirts, shirts, and makeup. He would lock his door and close the curtain on friday evenings when he knew his parents would be out. Then he would get dressed up in his cute clothes and play cheesy pop music through his speakers. It was fun, made him feel happy and safe. 

Once he was done admiring himself, Thomas turned to a smaller shoebox with women's magazines he had taken from the junk mail pile. Grabbing this week’s issue he flopped onto his bed, rolling on his stomach, legs bent in the air as he opened the booklet. It was fascinating to read these magazines. They offered so many tips that Thomas would never have thought of. The best washes for a clear face, the latest color palettes for summer, recipes for homemade face masks, and other such things. 

The boy sighed as he flipped through the pages. He wished he could buy the cute dresses and skirts the models wore. Or use all the products they did in order to get smooth perfect skin. But he couldn’t. Not yet. At least for the next year. Then he would be off to college, and would be able to dress up whenever he wanted. But not yet. Thomas pouted, now he was sad. Closing the magazine, the teen got up and headed over to his computer. 

Opening up the current summer mix, he pressed play, letting the music play over his speakers. Music helped him relax. He swayed and spun, dancing to the beat of the music. It was good music. Even though he would never admit to listening to it, he still enjoyed it deep down. His skirt swayed with his movements as he closed his eyes and just danced his heart away. 

Monday morning was when he met her. A tall girl, in his grade. She was new, just transferred to his school. She was beautiful. Short brown hair, kind eyes, lovely curves, thick thighs and of course a nice ass. Thomas couldn't help but stare as she laughed with some of his other classmates. He desperately wanted to talk to her, but his nerves stopped him from speaking up. However that didn’t last long. They had biology together. And she sat next to him. 

Thomas squirmed slightly in his seat, unable to keep from glancing over at her. “Hey, my name’s Lily.” She introduced, holding out a hand. He hesitantly shook it. “Thomas.” His voice was quiet and nervous. She was just so hot. He couldn’t help it. The girl smiled and took back her hand. “So, I guess I need a partner for this week’s assignment.” She humed. The teasing hint in her tone made Thomas’s cheeks flushed as she shifted, the calming feeling of silk under his jeans calming him. Good thing he decided to wear a pair of panties today. 

“Well...uh….I could be..y-your partner.” He offered, fumbling for words. The girl only shrugged. “Sure. I dont know many people here. First day and all.” She grabbed his hand and pulled it close so she could write her number on it. “Here. Just text me and we can talk.” Thomas felt his breath hitch. She was kind of strong. He could only nod as the bell rang and she left. 

Thomas sat blinking, still trying to think. It was hard. She was just so….perfect. He threw his books back into his backpack before hurrying out of the classroom. It was lunch, most of the students wandering about and talking while they ate, but Thomas couldnt see Lily. She must have left campus. He hurried into his math class and sat down to eat his lunch. As he was pulling out his food, he caught sight of the neat numbers on the back of his hand. 

He paused before pulling out his phone and typing out the number. But what should he say? Thomas chewed his lip.  
GrimHistorian to MythicBitch

GH: Hey its me, Thomas. 

He pressed send before he could regret it. Only a moment later he got a response. 

MB: Hey Thomas! 

GH: So how are you liking the new school?

It was a boring question, but Thomas couldnt think of anything else to say. He pull out his sandwich and ate it slowly as he watched his screen. 

MB: Its a bit different from my last school. But not bad. I kind of like it here.

GH: Yeah it is pretty different from most schools. Hehe

GH: But everyone here is super nice. I’m sure you’ll fit right in.

MB: Yeah I hope so! You are a lot nicer than most of the kids at my old school. And cuter.

Thomas almost choked on his sandwich. Did she really just say that?! He reread her words over and over. She really said that. His cheeks burned as he looked up to check if anyone else had seen his screen. Thankfully no one was behind him. Thomas turned back to his screen, cheeks still warm. 

GH: I guess so.

He shuttered softly, trying to ignore Lily’s previous statement. She didn’t text him back, Thomas didn’t mind. With a girl as hot as her, he was almost positive she would be busy talking to someone else. 

He was surprised when only two days later Lily asked him to be her partner for a project in History. Why would someone like her want to even interact with someone like him? Either way, she would be coming over in only a few minutes. Thomas made sure to hide all of his dress up stuff, so that no matter what happened she would never find it. 

Then there was a knock on the front door. Thomas exhaled and left his room. Lily looked beautiful. She wore a pair of casual leggings and a cute band tshirt, her smile tying everything together. “Hey Thomas. Are you ready to get started?” She asked, slipping past him and into the house. Thomas smiled shyly and closed the door. “Yeah. I’ll show you my room.” 

He led her into his bedroom, Lily looked around. “Wow this is a nice room.” She said warmly. Thomas nodded and headed over to his stereo system to put on some soft music. He hummed and bent over a bit. The cool air of his room brushing over his lower back. He would need to turn down the AC. Then Thomas froze. Lily chuckled darkly and the boy suddenly spun around. She was eyeing him dangerously. She took a step forward and he took a step back, his back hitting the wall. 

Thomas froze, his breath hitching in his throat as Lily leaned closer, her body pinning him against the wall. She was taller and stronger than him, there was no way he could escape. He swallowed thickly and forced back a whimper. Lily ran her free hand over his hip, pausing to play with the waistband of his jeans. So close to feeling the silky lace just underneath. Thomas’s body went rigid. No no no no no no. She couldn’t see him like this. What if she told everyone else? 

Fear grew in his gut, making it hard for him to breathe. Lily clicked her tongue and slipped her hand under his waistband, moving back to cup his ass through the material. “Look at that.” She almost purred, giving his ass a firm squeeze. Thomas gasped for breath, his knees going a bit weak. “Is the pretty boy wearing his special panties?” She asked, fingers still playing with the soft material. Thomas nodded, his cheeks red with shame. 

The taller girl licked her lips, pulling away. “Do you have anything else pretty boy?” She questioned, glancing around the room. Thomas had to answer, he feared that if he disobeyed she would spill. So he shamefully got down to pull the boxes out from under his bed. Three boxes in total, all small shoe boxes. Lily sat back on his bed, watching down at him while he pulled out the boxes. She raised her eyebrow when he looked up and Thomas quickly opened the lids revealing his magazines, makeup, and clothing. His cheeks burning with embarrassment. 

Lily was silent for a moment longer. “Is this all you have?” She asked in a harsh disbelieving tone. Thomas lowered his eyes in shame and nodded. It wasn't a lot, he did admit. But even this amount was hard to get. Lily leaned over and grabbed Thomas’s chin, forcing him to look up at her. “I’ll make a deal with you pretty boy.” He blinked, confused. 

“How about you become my little sugar baby, and in return, I’ll keep silent about all of this.” She hummed, glancing over to the boxes. Thomas paused, a sugar baby? He sort of knew what that meant, but not completely. “I’ll even buy you more pretty things to wear for me.” She added. The deal sounded too good to be true. Thomas swallowed and relaxed. “Alright. It's a deal.” 

Lily smiled and she released his chin. “Alright. Get up. We are going to the mall.” She ordered sharply, standing up off the bed. Thomas closed his boxes and rehid them before obediently standing up and following her out of the room. But what was he going to tell his mom? Somehow Lily had already thought about it, crossing the living room towards where his mom sat, watching tv. “Soo. Thomas offered to help me go shopping for my date next weekend. Do you mind if he comes with me?” She asked in her sweetest tone. 

His mother gave a grunt of approval, not even turning from the tv. Lily smiled and grabbed Thomas’s hand in a strong grip and pulled him to her car. It was making him excited, having this hot, strong woman pull and push him around. Thomas’s cock was already starting to get hard in his pants. Lily pushed him into the passenger seat and shut the door. In no time they were speeding down the main road towards the mall. 

“Alright. So as my sugar baby, you will have a few rules to follow.” Lily explained as she drove, not taking her eyes off the road. Thomas nodded, ready to hear what he had to do. “First rule: No dates without my permission. I don’t care if you see other guys or girls. Just ask before any dates. Second rule: I will be picking your outfits from now on. We are going to buy you a few new outfits and every morning I will tell you what to wear and I expect you to wear it with no complaints. Third rule: If you listen and are good, I will give you an allowance. Three hundred dollars a month. Every month I want you to pick out one outfit that you like and get it. The rest can be spent on whatever you want.” As she spoke, her fingers tapped on the wheel, a rhythm that matched her even paced speech. 

“Fourth rule: Once a week, we will go out and do something. Whether it's lunch, shopping, going to a movie, or whatever else. Every saturday you will spend the day with me. Feel free to suggest things you want to do. And my last rule, the most important rule of all of them. You must communicate with me. Tell me if I ever go too far, you don’t like something, or you don’t feel safe. I need you to communicate with me if this is going to work.” She shifted to rest a hand on his thigh. Thomas felt himself relax under her touch. It felt nice. His cheeks warmed as he nodded in acknowledgment. “O-ok. That doesn’t sound too bad.” 

Lily smiled and finally pulled into the mall parking lot. By now Thomas was a lot more at ease. Honestly, it didn’t seem too bad that Lily knew about him and his secret hobby. They pulled into a good parking spot up front and Lily climbed out. “Come on. Let’s get going. I have a friend I want you to meet.” She smiled, grabbing Thomas’s hand and leading him inside. He couldn’t keep the smile from his own face, quickening his pace to keep up with her. 

The mall was huge. Thomas had only been in it once with friends who wanted to see a movie in the theater that was attached. It was a huge semi circle with two stories and a glass roof. Brilliant sunlight streamed into the area, making the floor glitter and the sleek glass shine. Since it was a friday, the place was already kind of crowded. But Lily didn’t seem to mind. She led Thomas towards one of the nearby stores, her hand warm in his. 

It was a dimly lit store, with catchy pop music playing over the speakers. Clothes hung on racks or sat folded on shelves. Mainly jeans and tshirts to match the modern punk movement. Thomas didn’t think he would look good in any of this. However Lily led him right past the clothes and to the cashier where a bored looking teen sat on her phone. She had short black hair with a red stripe down the side. The teen had snake bite piercings and wore heavy dark eyeliner. 

Lily smiled. “Hey Mari! Guess what.” She chirped, pulling Thomas over to the counter. The teen looked up, first at Lily then at Thomas. She raised a dark eyebrow. Lily sighed and rolled her eyes. “I got a new sugar baby.” She explained. Thomas’s cheeks went pink and he looked down at his feet. Mari nodded knowingly. “Take him to the back. I’ll get Kie to cover for me.” She explained, slipping her phone into her jacket pocket. 

Thomas was dragged towards a back door that read, “Employees only.” Lily ignored the sign and entered the backroom. It was more of a staff lounge with a few lockers and an old couch. The walls were painted a dark black to make the room seem dimmer. Lily finally let go of Thomas’s hand, turning to look at him. “Alright so, Mari is going to help us size you properly and find some colors that will look good on you.” 

As she spoke she started to unbutton Thomas’s shirt causing him to panic and try to step back. The girl shot him a look. “Hold still. You need to be stripped so she can get a more accurate size.” Lily explained, finishing the last button before pushing the shirt off his shoulders. He was immediately self conscious. Thomas didnt have much muscle, or any real fat on him. He was about as thin as a pole and just as tall. Lily didn’t seem to care. 

Her warm hands brushed against his sensitive skin as she started to undo his pants. She helped him kick out of his boots then pants, leaving Thomas bare in the slightly cool room. He felt awkward and unsure, standing there in nothing but his socks and a pair of baby blue panties that hugged his hips and ass. Lily bundled up his clothes and left them on the couch. She then moved him to a curtained off area of the back room where there was a small elevated block and a huge mirror. Thomas avoided looking at himself in it. 

Lily gave him a warm smile that calmed him slightly before she left him in the curtained off area, standing on the elevated box. Thomas waited, rocking slightly on his feet. Then the sound of a door. A lock clicking into place. “So. Tell me about what you need.” Mari drawled. The sound of a locker swinging open and things moving around. “Well, we are looking for more feminine clothing. Nothing too frilly for now. Just a few outfits he can wear out in public without too many people commenting.” Lily explained. 

Thomas could feel the shame rise in his gut. Why was she so casual in telling about his darkest secret. Mari only hummed before pushing aside the curtain. She had a fabric measuring tape and a large book. Lily was casually laying across the couch, her eyes watching. If Mari was surprised by the panties Thomas wore, she didn’t let it show. Instead she almost looked indifferent to it. “What about making him look more girl-like? Or even androgynous?” Mari asked as she grabbed Thomas’s arm and moved it. Her grip was firm, moving him where she needed to. Thomas let her, wanting this to be done as soon as possible so he could get dressed again. 

Lily hummed in thought. “What do you think Thomas?” She asked, surprising him. Did she really want to know his opinion? Thomas hesitated. “M-maybe a-a-androgynous.” He forced out, stumbling over his words. Lily only nodded. “That could work. What were you thinking Mari?” The dark haired teen stayed silent for a moment, wrapping and pressing the tape over various spots on Thomas’s body. “Lower cut shirts. Cropped stuff. Skirts with leggings or tights.” She mused as she measured around his hips then chest. 

“But he definitely needs to eat something. It would help add some curves to help with the look.” Thomas swallowed and tried to hold still. He knew he was thin. But he never really thought about putting on weight on purpose. Lily got up from the couch and crossed over to where the two were. “What materials were you thinking?” She asked, looking over Thomas’s body. Mari paused in her measuring, tilting her head. Now it was close to impossible to not squirm. It felt odd having these two hot as hell girls look at his body like this. Thomas felt like he was some sort of lab rat being observed under a lens. 

“Probably a blend of pastels with blacks. As much as the blacks will make him look like even more of a stick. If you place them well enough, it might give the effect of curves.” Mari pointed out before setting her tape aside. She looked up at Thomas and smiled warmly. “Here, you can get dressed again.” The girl held out a hand to help him down and Thomas did so obediently. As he dressed, the two girls chatted about fabrics, brands, styles, stores, and other things that made Thomas’s head spin. 

By the time he was buttoning up the last button on his shirt, Lily was hugging Mari goodbye. The store worker smiled and gave Thomas a wave before Lilly pulled him out of the room and back into the store. He was thankful to be out of that dark room. “Alright. Let’s get something to eat. I’ll explain my plan over some food.” She said as she pulled him towards the food court. Thomas couldn’t help the smile that returned to his lips. Despite the awkward start, he wanted to make the most of this. 

Lily brought them over to a sushi shop and ordered for both of them. Thomas didn’t really mind. He wasn’t usually a picky eater. Once they got their food, Lily led them over to a booth in the corner. “Alright. So here's what I'm thinking.” She hummed, opening the lid to one of the sushi boxes. Now that it was all on the table, it was quite a bit of food. Thomas got out his chopsticks and started to eat as he listened. 

“I said I was going to help you with this. So for the most part I’m in charge. If anything is uncomfortable or you don’t like it, just tell me.” She pointed her sticks at him. “Today we are just going to get some of the baseline stuff done. Stop me if it's too much.” Lily paused to eat some of the sushi. “Today I was thinking we get your nails done. No color just yet, just clean them up. Then a haircut. After that we’ll pick out a few outfits and some makeup.” 

Thomas nodded. It didn’t seem too bad. Lily kept going. “Now here is some of the more extreme stuff I definitely need to know you are ok with before continuing.” She sat back. “Probably not today, but soon. So, what do you think of a full body wax and a tan at one of those salons?” She asked. Now that was a bit harder. Thomas set down his sticks to think for a moment. He only ever wore long sleeves and jeans at school, no one would really notice if he got waxed. And maybe if he got a tab, he would look less like a ghost. 

Thomas shifted in his seat and gave a shy smile. “Actually, that would be nice.” He said, looking down at his food to hide his embarrassment. Lily squealed happily. “Wonderful! I’ll set up appointments as soon as possible.” She pushed one of the sushi trays closer to him. “Now eat up then we will go shopping.” Thomas nodded and started to eat. It was more than he usually ate, but for some reason, deep down, he wanted to make Lily happy. 

After they completely destroyed the food, Lily started to lead them to the beauty section of the mall. There were more girls in this area. Thomas felt awkward at first, but Lily’s carefree attitude made him relax. If she wasn’t worried, why should he? The first shop they entered was a nail salon. There were a few girls already in chairs, chatting with the workers. Lily pulled him over to the front desk. 

“Two fulls please. Just a clear protective coat, no color.” She told the lady, pulling a card out of her wallet to pay. The lady only nodded and led them to different tables. Now Thomas’s nerves were starting to return. He was alone now, sitting across from a sweet looking lady. What was she thinking of him? The lady seemed to notice his sudden discomfort. “Hands darling.” She hummed, pulling his hands closer on the towel. Then she got to work as if he was just another customer. 

This helped Thomas to get more comfortable. Thankfully the lady didnt talk as she filed and trimmed his nails. Thomas spent that time thinking. No more than two hours ago his life felt like it was ending. Now he felt the most alive he had in years. It was nice being able to get his nails done without having to worry what other people would think of him. If Lily didn’t care, then neither did he. 

Once the lady was done with his nails, she led him over to one of the chairs and made him take off his shoes so he could soak his feet in the warm water. To his relief, Lily sat down in the chair next to him. She smiled and reached over, he gave her his hand to show her his nails. “That looks a lot better. We might pick up some lotion for your hands as well. That way they can get smooth.” She explained before sitting back and slipping off her shoes. 

While they got their nails done, Lily and Thomas talked. He told her about his favorite songs and singers while she explained to him the plot of her all time favorite movie. By the time they were done, Thomas felt even more relaxed around Lily. She got him a few bottles of nail polish and a bottle of fancy hand lotion before they left to go get his haircut. 

“So it won’t be anything crazy. Just to neaten it up a little.” She explained, leading him towards the other salon. Thomas didn’t mind, so far she had made decisions he had agreed with. So he trusted her. The hair salon was a little less crowded and a lot more peaceful. Lily explained to the desk lady what they wanted. Then Thomas was pulled towards one of the chairs by one of the ladies. 

Lily sat by the desk in one of the waiting chairs, chatting to the desk lady about different products. Thomas closed his eyes and let them work on his hair while he listened to Lily’s nice voice. It was pleasant and he felt peaceful. This was what he always wanted. What he knew he deserved. He deserved to feel nice and beautiful. To feel cared for. 

The haircut didn’t last long. Thomas didn’t even notice the difference at first, only that it was cleaned up to make him look more put together. Then he was sent back to Lily who was paying for a few different hair products. The lady smiled as she bagged them, slipping in a small instruction sheet so Thomas knew what order to use all the bottles. 

Now was the exciting part. The part Thomas had been looking forward to all evening. Lily led him back towards the main part of the mall. “Come on. I want to hit as many stores as we can so that we can figure out what will work best for you.” She explained before pulling him into a shop. 

Thomas had to admit. Lily definitely knew what she was doing. So Thomas just gave in and let her shove outfits at him for him to change into. He tried on tight shirts and baggy shirts, leggings and tights, skirts and shorts. It was all a blurry haze of soft fabrics and flowy material. Until finally Lily was satisfied. They had gone through most of the stores and found at least ten outfits, Thomas’s arms heavy with bags. 

But by the end, he was smiling and giggling with Lily as they finally left the mall. By now the sun had long since set, leaving the sky dusted in stars. “I had a lot of fun. Thank you for taking me out.” Thomas said as he slid into the seat. He had changed into a pair of black leggings and a pastel blue cropped hoodie. Lily started up the car and turned towards Thomas’s house.

“Of course! I'm glad you had fun. When I get home I’ll set up the appointments for the tan and wax.” Thomas nodded and relaxed into the seat. The drive back to his place was pleasantly quiet. Then Lily was in front of his house. “Here. Before you go.” She reached into her wallet and pulled out a silver card. It had his name stamped in blue on the front. “I’ll put your allowance on here. You can use it for whatever you want. Just pick a pin number when you first use it.” She explained. Thomas took the card and carefully slipped it into his hoodie pocket. 

Lily gave him a brilliant smile as he thanked her and grabbed his bags out of the back seat. Then she was gone into the night. Thomas sighed and turned to go inside. His mom’s car was gone so he didn’t need to worry about hiding the bags as he unlocked the door and headed to his room. He set down his bags and made sure to lock his door. Not that he needed to. 

Today had been perfect. But now Thomas was tired and sore from walking around. He kicked off his shoes and started to pull that clothes from their bags. There wasn’t enough room in the shoeboxes under his bed, so Thomas just shrugged and hung them up in the closet. He set all the different bottles in the bathroom that connected to his room then collapsed on his bed. 

As he lay he felt the poke of the card in his pocket. He pulled it out and rolled over on his side, looking at the shimmering silver with the neat dark blue text. Curious he pulled out his phone and downloaded the app for the bank that was used with the card. He created an account and added the card. When he checked his balance he saw the neat green print that read 300$. 

He felt a wave of relief at the number. Now he wouldn’t have to worry about needing to borrow money from his mom. This would also help his savings for when he finally moved out. Thomas sighed and put the card in his own wallet before falling back into the bed, this time snuggling under the covers. _Bzzzzz_ His phone screen lit up. 

MB: I got you an appointment for next saturday. We can do that for our hang out day. I’ll count today as a hang out day as well. See you Monday! 

Thomas smiled and turned off his phone. Still the best day ever. He started to drift off, thinking of all the things he would do with 300$.

**Author's Note:**

> Feedback is always welcome.  
> Let me know if anyone wants to see more of this!


End file.
